[Potential cardiotonic agents. 10. Synthesis and positive inotropic action of 5-(4-pyridinyl)- and 5-phenyl-substituted 2-alkylthio-3-cyan-pyridines and their S-oxidation products].
The alkylation of the 5-(4-pyridinyl)- and 5-phenyl-substituted 3-cyan-2(1H)-pyridinethiones 1 with alkyl iodides and halomethylcarbonyl compounds led to the 2-alkylthio-pyridines 3a-c, 3e, 3f and the thieno[2,3-b]pyridines 4, respectively. In an other way the 2-ethylthio-5-(4-pyridinyl)pyridines 3b and 3d were formed from the corresponding 2-chloroderivatives and ethylmercaptan. By means of oxidation of the 2-alkylthio-pyridines 3 with 3-chloroperbenzoic acid and potassium permanganate, respectively, the 2-sulfinyl- and 2-sulfonyl-pyridines 5 and 6 were obtained. The 3-cyano-5-(4-pyridinyl)pyridine-2-sulfonic acid 7 was prepared by oxidation of the 2(1H)-pyridinethione 1a with potassium permanganate. Some derivatives possess positive inotropic properties.
Rumler
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Akademie der Wissenschaften, DDR, Institut für Wirkstofforschung, Berlin.
Hagen
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Hagen
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D000818:Animals; D002316:Cardiotonic Agents / Q000138:chemical synthesis* / Q000494:pharmacology; D055598:Chemical Phenomena; D002627:Chemistry, Physical; D006168:Guinea Pigs; D066298:In Vitro Techniques; D009200:Myocardial Contraction / Q000187:drug effects; D009570:Nitriles / Q000138:chemical synthesis* / Q000494:pharmacology; D011725:Pyridines / Q000138:chemical synthesis* / Q000494:pharmacology; D013329:Structure-Activity Relationship; D013871:Thiones / Q000138:chemical synthesis / Q000494:pharmacology
D002316:Cardiotonic Agents; D009570:Nitriles; D011725:Pyridines; D013871:Thiones
Potentielle Kardiotonika. 10. Mitteilung3: Darstellung und positiv inotrope Wirkung von 5-(pyrid-4-yl)-und 5-phenyl-substituierten 2-Alkylthio-3-cyanpyridinen und ihren S-Oxidationsprodukten.